Total Synthesis of Myceliothermophins C, D, and E
The total synthesis of cytotoxic polyketides myceliothermophins E (1), C (2), and D (3) through a cascade‐based cyclization to form the trans‐fused decalin system is described. The convergent synthesis delivered all three natural products through late‐stage divergence and facilitated unambiguous C21...
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| Published in: | Angewandte Chemie International Edition Vol. 53; no. 41; pp. 10970 - 10974 |
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| Main Authors: | , , , , , , |
| Format: | Journal Article |
| Language: | English |
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06-10-2014
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| Abstract | The total synthesis of cytotoxic polyketides myceliothermophins E (1), C (2), and D (3) through a cascade‐based cyclization to form the trans‐fused decalin system is described. The convergent synthesis delivered all three natural products through late‐stage divergence and facilitated unambiguous C21 structural assignments for 2 and 3 through X‐ray crystallographic analysis, which revealed an interesting dimeric structure between its enantiomeric forms.
Cascades: The total synthesis of the cytotoxic myceliothermophins C, D, and E have been achieved through a sequence involving a cascade bis(cyclization) of epoxide or aldehyde substrates to forge a trans‐fused decalin precursor of the natural products. |
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| AbstractList | The total synthesis of cytotoxic polyketides myceliothermophins E (1), C (2), and D (3) through a cascade‐based cyclization to form the trans‐fused decalin system is described. The convergent synthesis delivered all three natural products through late‐stage divergence and facilitated unambiguous C21 structural assignments for 2 and 3 through X‐ray crystallographic analysis, which revealed an interesting dimeric structure between its enantiomeric forms.
Cascades: The total synthesis of the cytotoxic myceliothermophins C, D, and E have been achieved through a sequence involving a cascade bis(cyclization) of epoxide or aldehyde substrates to forge a trans‐fused decalin precursor of the natural products. The total synthesis of cytotoxic polyketides myceliothermophins E ( 1 ), C ( 2 ), and D ( 3 ) through a cascade‐based cyclization to form the trans‐fused decalin system is described. The convergent synthesis delivered all three natural products through late‐stage divergence and facilitated unambiguous C21 structural assignments for 2 and 3 through X‐ray crystallographic analysis, which revealed an interesting dimeric structure between its enantiomeric forms. The total synthesis of cytotoxic polyketides myceliothermophins E (1), C (2), and D (3) through a cascade-based cyclization to form the trans-fused decalin system is described. The convergent synthesis delivered all three natural products through late-stage divergence and facilitated unambiguous C21 structural assignments for 2 and 3 through X-ray crystallographic analysis, which revealed an interesting dimeric structure between its enantiomeric forms. |
| Author | Pattanayak, Manas R. Ioannidou, Heraklidia A. Lu, Min Shi, Lei Shah, Akshay A. Lamani, Manjunath Nicolaou, K. C. |
| AuthorAffiliation | Prof. Dr. K. C. Nicolaou, Dr. L. Shi, Dr. M. Lu, Dr. M. R. Pattanayak, Dr. A. A. Shah, Dr. H. A. Ioannidou, Dr. M. Lamani, Department BioScience Research Collaborative, of Chemistry, Rice University, 6100 Main Street, Houston, TX 77005 (USA), kcn@rice.edu |
| AuthorAffiliation_xml | – name: Prof. Dr. K. C. Nicolaou, Dr. L. Shi, Dr. M. Lu, Dr. M. R. Pattanayak, Dr. A. A. Shah, Dr. H. A. Ioannidou, Dr. M. Lamani, Department BioScience Research Collaborative, of Chemistry, Rice University, 6100 Main Street, Houston, TX 77005 (USA), kcn@rice.edu |
| Author_xml | – sequence: 1 givenname: K. C. surname: Nicolaou fullname: Nicolaou, K. C. email: kcn@rice.edu organization: Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA) – sequence: 2 givenname: Lei surname: Shi fullname: Shi, Lei organization: Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA) – sequence: 3 givenname: Min surname: Lu fullname: Lu, Min organization: Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA) – sequence: 4 givenname: Manas R. surname: Pattanayak fullname: Pattanayak, Manas R. organization: Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA) – sequence: 5 givenname: Akshay A. surname: Shah fullname: Shah, Akshay A. organization: Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA) – sequence: 6 givenname: Heraklidia A. surname: Ioannidou fullname: Ioannidou, Heraklidia A. organization: Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA) – sequence: 7 givenname: Manjunath surname: Lamani fullname: Lamani, Manjunath organization: Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA) |
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| Copyright | 2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Wiley-VCH verlag GmbH & Co. KGaA, Weinheim |
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| Issue | 41 |
| Keywords | cascade reactions natural products decalin total synthesis polyketides |
| Language | English |
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| Notes | Bristol-Myers Squibb ArticleID:ANIE201406815 Rice University istex:57311F5D32400C422835D3216935C33F73695CEC National Institutes of Health - No. AI0055475 ark:/67375/WNG-TK3FCNJH-3 The Cancer Prevention & Research Institute of Texas (CPRIT) European Commission Financial support was provided by The Cancer Prevention & Research Institute of Texas (CPRIT), the National Institutes of Health (USA) (grant AI0055475), the National Science Foundation, and Rice University. Fellowships to M. Lu (Bristol-Myers Squibb) and H.A.I. (Marie-Curie International Outgoing Fellowship, European Commission) are gratefully acknowledged. National Science Foundation Financial support was provided by The Cancer Prevention & Research Institute of Texas (CPRIT), the National Institutes of Health (USA) (grant AI0055475), the National Science Foundation, and Rice University. Fellowships to M. Lu (Bristol‐Myers Squibb) and H.A.I. (Marie‐Curie International Outgoing Fellowship, European Commission) are gratefully acknowledged. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
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| Snippet | The total synthesis of cytotoxic polyketides myceliothermophins E (1), C (2), and D (3) through a cascade‐based cyclization to form the trans‐fused decalin... The total synthesis of cytotoxic polyketides myceliothermophins E (1), C (2), and D (3) through a cascade-based cyclization to form the trans-fused decalin... The total synthesis of cytotoxic polyketides myceliothermophins E ( 1 ), C ( 2 ), and D ( 3 ) through a cascade‐based cyclization to form the trans‐fused... The total synthesis of cytotoxic polyketides myceliothermophins E ( 1 ), C ( 2 ) and D ( 3 ) through a cascade-based cyclization to form the trans-fused... |
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| SubjectTerms | Biological Products - chemical synthesis Biological Products - chemistry cascade reactions Crystallography, X-Ray Cyclization decalin Molecular Conformation Naphthalenes - chemistry natural products Nitrobenzoates - chemistry polyketides Polyketides - chemical synthesis Polyketides - chemistry Stereoisomerism total synthesis |
| Title | Total Synthesis of Myceliothermophins C, D, and E |
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